I wish there was this for regular clothes. I virtually never go out and buy clothes (lack of time, interest etc.) until my old ones starts to wear, it's pretty much a maintenance thing for me. I'd just like to put in my measurements, maybe rate a few clothes I so it knows what I like and then have stuff magically appear every now and again. I'm sure a random fashionable person would improve my looks by actually having taste. :P
http://shirt.woot.com is nice for T's at least but I don't think it would work well for anything more expensive or less expressive than that.
I actually worked on a site that did this way back in 1999.
It's hard because people get fatter and skinnier all the time (usually just fatter) thus, the clothing "refill" doesn't work. Especially for pants. In fact, most men only bought new pants because of a size change, not because their old ones wore out. It works for socks because people's feet don't change.
Another problem is that even for men, standard sizes aren't standard at all. A size 32 waist pants from Old Navy is about a size 38 in Levi's 501. Athletic cut dress shirts are much larger than slim cut dress shirts in the exact same size. For women, you can multiply this situation by the number of retail stores and brands in the world. Sizes even change in the same line from season to season. Finally, people lie about their waist size, even to their computer.
When I decide that my old clothes are worn/stained/horribly unfashionable and set out to refresh the wardrobe a bit, I set out to buy a few new ones. After settling on which store to patronize (Am I too old for AE et al.? Am I too young for Brooks Brothers? Would I be just as happy with something from Target?), I go to that store. At that point, I browse around for a bit, get overwhelmed by the number of options, become unsure about what would look good (or even what's in style), and leave without buying anything.
I'd really like to see some sort of online or in-store system with a super-simple way of finding new clothes. Maybe three variables: age, desired style (hipster? MBA? stereotypical engineer?), and body type. The output could be something like, "OK, buy this, this, and that. You'll look good."
This is difficult for a number of reasons. As I mentioned in a previous post, the big reason is that sizes are not standardized. A size 32 waisted pant can be a true size 32, or really a size 38. Also, people's sizes fluctuate, usually increasing.
The 2nd part of your question, simply defining what style of clothing to wear is even more difficult and probably impossible to automate. However, there are professionals you can hire which will solve the problem for you. It's not cheap, but if you're single and make a good programming salary it may be a better investment than the latest digital camera or gaming system.
I think this is an idea that enough people that have had that I'm surprised nothing like it has come out. A few months ago some people launched a site like this for interior decorating. I asked if they were going to do it for clothing and they said it wasn't a focus because the margins/affiliate payments for interior decorating are so much better.
You should be sending any clothes you buy to a tailor regardless of how you buy the clothes. Further, you can't buy clothes off the rack without trying them on! Skin tones are different and you really need to try the clothes on.
I'm a student so going to a tailor is out of the question although I'm not so sure I'd even think of that on my own if I had bundles of money. I guess I should try that sometime.
I've been fairly happy with the clothes I've bought by mail order though, there's been a few snags sure but you can send them back and it tends to be cheaper. I do go to the store sometimes, especially for jeans as it's hard to find pairs that fit me since I've got skinny long legs.
As for the skin color thing, I can honestly say that I have no idea whatsoever on how to judge that.
http://shirt.woot.com is nice for T's at least but I don't think it would work well for anything more expensive or less expressive than that.